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What to Do in Chicago in the Fall

This blog post was updated on November 2, 2018.


After being in Chicago in the thick humidity of summer, when clothes start to stick to you after you step foot outdoors, fall is a welcomed change.

Instead of melting, the people of the city bundle up in cozy sweaters with scarves and hats to indulge in the daytime sun that highlights the autumn colors overtaking the trees.

Indeed, for visitors arriving on flights to Chicago, Fall is a comfortable time in the city.

We’ve already covered some of the best things to do in Chicago, but this list is going to focus on the things to do in Chicago in the fall, beyond the ghost tours and deep dish pizza.

The weather may be brisk, but I urge you to take it to the streets, or even down to the farmers markets.  Fresh veggies in all your favorite autumn flavors will be ripe, so be sure to grab some apples, squash or sweet potatoes to fix up a proper fall meal (if you have cooking facilities in your accommodation).  Walking around the markets on their own is a cultural experience as it lets you get face-to-face with the people that live and work in this great city.  For a list of farmers markets in Chicago, visit this site.

Nothing says, “Welcome to the Midwest,” quite like corn (trust me, I grew up there), so what better way to get a real Midwestern cultural experience than to find your way through a corn maze.  Outside of the city in Maple Park, the Kuipers Family Farm plays home to a giant maze… through a corn field.  You better act quick as the maze is only open through September and October when the corn stalks are at the end of their life.

Chicago features some of the country’s best museums.  You can beat the fall chill (or rain on some days) by walking into one of these:  the Museum of Contemporary Art, the Art Institute of Chicago, the Field Museum of Natural History and the Adler Planetarium.  The zoo, located in Lincoln Park, is the educational experience that family members of all ages can enjoy.

Head down to Michigan avenue for a walk and a bit of window shopping.  When you’ve worked up an appetite, a big bread bowl soup will offer a warm and filling meal.  Several of the eateries in the vicinity should offer up the soup, salad and sandwich type combos we know and love well.

When all else fails, a bus tour of Chicago can get you around to all the best sights with little or no fuss.  Sometimes the weather dips down to an uncomfortable cool, so a bus tour would be perfect for the temperature.  Plus, the extra bits of history and insight provided from your guide can provide a whole new perspective of the city of Chicago.  They are an invaluable resource!

Overall, I would say that Chicago is a city with just as much possibility as a travel destination in fall as in spring or summer.  Winter, on the other hand, is another story.

You might also be interested in reading about some of the iconic Chicago attractions.

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